N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester
• CAS No.: 1421282-45-2
• Molecular Formula: C₁₈H₂₆FNO₆
• Molecular Weight: 371.406
• Mol file: 1421282-45-2.mol

Synonyms:N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester

Chemical Property of N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester

There total 7 articles about N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

C18H26AgNO6 → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester (1421282-45-2)

Guidance literature:

With Selectfluor; In acetone; at 20 ℃; for 0.5h; Molecular sieve;

DOI:10.1039/c2cc38646a

Reference yield:

C18H26AgNO6 → (S)-ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate (128217-62-9) + N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester (1421282-45-2)

Guidance literature:

With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); In acetone; at 20 ℃; for 0.5h; Overall yield = 35 %; Molecular sieve;

DOI:10.1039/c2cc38646a

Reference yield:

(S)-ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate (128217-62-9) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester (1421282-45-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis-[(trifluoroacetoxy)iodo]benzene; iodine / dichloromethane / 3.25 h / 0 - 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 17.17 h / 80 °C / Inert atmosphere

3.1: sodium hydroxide / methanol / 3 h / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

4.1: 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) / acetone / 0.5 h / 20 °C / Molecular sieve

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; iodine; potassium acetate; 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); bis-[(trifluoroacetoxy)iodo]benzene; sodium hydroxide; In methanol; dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1039/c2cc38646a

upstream raw materials:

(S)-ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-iodo-4,5-dimethoxyphenyl)propanoate

N-(tert-butoxycarbonyl)-3,4-dimethoxy-6-(1,3,2-dioxaborinane-5,5-dimethyl)-L-phenylalanine ethyl ester